Methoxyacetyl chloride → HCID 68935337, compound

HRID 81894Notes

Reaction equation

HRID 81894 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=O.[NH2:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[NH:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[N:15][CH:14]=[CH:13][CH:12]=2>N1C=CC=CC=1>[CH3:1][O:2][CH2:3][C:4]1[N:18]([CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])[C:17]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=1

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 22172710tert-butyl N-{2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethyl}carbamate

Product 1

HCID 68935337HCID 68935337, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methoxyacetyl chloride (5.9 g, 54 mmol) was added dropwise to a chilled (ice bath) solution of tert-butyl N-{2-[(3-amino[1,5]naphthyridin-4-yl)amino]ethyl}carbamate (15.0 g, 49.5 mmol, U.S. Pat. No. 6,194,425, Example 87) in anhydrous pyridine (100 mL). The reaction mixture was heated at reflux until analysis by liquid chromatography/mass spectroscopy (LCMS) indicated that the reaction was complete. The reaction mixture was concentrated under reduced pressure. The residue was diluted with ethanol (100 mL), combined with potassium carbonate solution (200 mL of 2 M), and heated at reflux for 4 hours. The reaction mixture was cooled and then concentrated under reduced pressure. The residue was partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane. The combined organics were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to provide 14 g of tert-butyl N-[2-(2-methoxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]carbamate.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux until analysis by liquid chromatography/mass spectroscopy (LCMS)
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionThe residue was diluted with ethanol (100 mL)
  5. temperatureheated
  6. temperatureat reflux for 4 hours
  7. temperatureThe reaction mixture was cooled
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was partitioned between water and dichloromethane
  10. extractionThe aqueous layer was extracted with dichloromethane
  11. dry with materialThe combined organics were dried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d98f097c3b2e4b70b41af9b04ea091d2
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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